It won't happen if Aoki is lucky. Penn's takedown defense is absolutely phenomenal and his boxing is way too good for Aoki. Even if Aoki could pull guard, there's no way I think he could submit Penn.
Penn is too good for him. Aoki will have no chance to bring him down, and even if he pull guards, he wont sub Penn from his back. Penn will kill him with his boxing
I would go as far to say that Penn's JJ is better than Aoki's. Aoki is an awesome grappler. Head to head just pure grappling it may be a toss up but in MMA Penn is way more versatile. His stand up is a killer and the likelyhood would be a Penn KO. Aoki has no striking to speak of. His dexterity much like Penn is great to watch.
Would be the best grappling match you'd ever see. I bet Aoki could still pull rubber guard whilst Penn held him in a Omoplata.
Penn is just so far ahead in striking and stopping takedowns that Aoki would have huge problems. Even on the ground is not exactly a great place to be for Aoki; Penn is better at fundamentals than Aoki, even if Aoki has a trickier game at this point. If you watch BJ's run to the Mundial championship he was really more of a smothering top game for points type of guy, which added with the additional depth of skill he has gained since then and the ability to GnP would spell trouble for Aoki assuming the fight does go to the ground.
If BJ were fighting who Aoki was fighting, hed seem tricky too with the rubber guard..but hed probably prefer knocking them out standing. Its a simple dilemma BJJ - BJ Striking - BJ by miles